The Assassins Lost Her Mark
by lilyben
Summary: The life of Lily Benedict was a simple, but cruel one. The greatest assassin to ever have lived, trained by Lucifer himself, didn't have many problems she couldn't handle. The job, she had been assigned, was that of The Winchesters. As always, kill them, and leave no traces. Why their lives were to end? She did not know. But one thing that gave her a hint as to how big this was.
1. Chapter 1

The Assassins Lost Her Mark - Chapter 1

The life of Lily Benedict was a simple, but cruel one. The greatest assassin to ever have lived, trained by Lucifer himself, didn't have many problems she couldn't handle.

The job, she had been assigned, was that of The Winchesters. As always, kill them, and leave no traces.

Why their lives were to end? She did not know. But one thing that gave her a hint as to how big this was, was the fact that the whole reason she was born and raised the way she was, was so that the brothers would be killed.

Omaha, Toronto. One of Americas many states. The bus slowed at its destination, and the windows displayed what little of an area it was. Just a couple of houses, here and there. Clearly, they where on the outside of town. The nothingness showed how the town wouldn't be much, itself.

Walking past the tourists information cabin, Lily spotted a few cameras, dotted around the perimeter of the building.

And that, she realised, her work would be easier than expected.

The motel she'd booked into was a sad, rundown place. Wallpaper peeling off the walls, light bulbs burst - she'd rather sleep in a car to here, but it was necessary. Sam and Dean Winchester had crashed here, so so would she.

She'd gained the information about where they were sleeping, through the man at the desk. He was old, and frail, and liked to talk a lot, so it wasn't very hard to get the information.

It wouldn't be as easy to find out where they'd gone following, though. She'd have to hack all the security cameras around the town, to keep an eye on them, and then find a way to casually earn their trust.

She was leaning more towards a hunter, who'd spotted a hunt around here, and decided to check it out. Probably work, but it'd take time since hunters are really cautious of others. Time, was what she didn't have.

Perhaps an inconspicuous, 18 year old, girl (which she was), who is really good at kicking ass? Seduce them with her mysterious personality. She laughed, she'd basically be playing the character of herself.

Later, Lily told herself. It isn't important at the moment.


	2. Chapter 2

Logging onto her laptop, she quickly brought up all the cameras in the vicinity. An easy task, which had been completed many times, prior.

She knew what she was looking for. Their picture had practically been burned into her brain, the amount of times she'd seen it; a 6'4, shoulder length hair, law student, and a slightly smaller, leather wearing, college drop out.

They walked right in front of the security camera facing the movie theatre. Who knew that would be their fatal mistake? In a flash, she was up off the bed, and prepping for their encounter.

Grabbing her shotgun, she checked herself out in the mirror, making sure her clothes were suitable for her character - combat boots, a short, black, floaty, skirt, a white, slim-fit, crop top, a leather jacket, and her hair in french plaits. Perfect. Dean wouldn't be able to resist.

Hiding her gun on herself, she checked she had the locket around her neck. Never had she forgotten it, but today was a big day. She wouldn't want to lose it now.

Driving towards the forest, in the Land Rover she had stolen, because it fitted her character, Lily spotted a side road that ended in a dead end. That was where she was to hide until the Winchesters arrived, which would be soon.

She knew exactly what was going to happen. The reason she was trained for this in the first place, was because of the prophecy that had been for told, in the ripped out pages of the Bible, that had been obtained by the demons and brought to Hell. It had said:

 _John Winchesters son,_

 _Will break the sixty-sixth seal,_

 _And free the angel from Hell._

 _He who loved his father so._

 _Even, this son, will be thy downfall,_

 _For the apocalypse shall end,_

 _With demons running,_

 _And Lucifer shall be slain._

Written long before time was created, these words where a puzzle to humanity. It brought joy to some, and terror to others. Eventually, when the events started to play out, and Lucifer was cast down for loving his father too much, heaven took an interest. But they were too late. Lillith, the first human to be turned to a demon, had found the page, which had not been memorised or rewritten, and dragged it back to Hell.

That was when the idea of Lily, was created. A child, born and raised for the purpose of denying Lucifers destiny. Named after the first demon, she was trained by Lucifer himself, became the greatest assassin, to kill them before it ever happened.

The only problem, was that they didn't know which brother it was.


	3. Chapter 3

There it was. The '67 Chevy Impala they drove everywhere in. She waited for them to drive around the corner and followed straight behind them.

Approaching them, Lily spotted a couple of other, unknown faces, who seemed to be here for the same reason as the boys; to find the thing that killed the campers.

Sam and Dean both noticed her at the same time. Taking a deep breath, she stepped out of the car and changed into character.

"Who are you?" Sam asked her, the first to speak, as Dean was just looking at her in awe.

"Lily Benedict. I've come to help look for the missing campers." Just like that, it slipped out. Her real name was just plastered there for everyone to see. No changing it now. She doubted they'd recognise it - she was careful how publicised she became.

Why not? she thought. This was her big day. Once killed no one would ever hear her real name again. Why not make use of it for once in her life?

"Nice to meet you. I'm Sam and this is my brother, Dean." His hand was outstretched but before she could take it, Dean stepped in front of him.

"Enough of my brother, you're way out of his league. I'm Dean Winchester, and you are hot as." He said, smirking as his eyes ran over her body. She felt a little tingle as he did so, but ignored it as usual. Emotions were _never_ to get in the way.

A loud sigh came from Sam, which signified he wanted to get going, and they headed off into the mysterious forest.

They all wandered through the trees, occasionally calling the named of the missing. As the other three people pulled on ahead, Dean and Sam both drew back and started keeping the same pace as Lily.

Here we go.

"So." said Sam.

"So." she replied, looking at him expectantly.

"Are you really here to find the people or for the…the thing…"

Before she could reply there came a scream from ahead. It had found them. The boys were going to get their answer soon enough.

Pulling her gun out, she sprinted to where the others were. The guy, a park ranger, was shooting into the bushes.

"Stop!" she shouted, as the brothers caught up.

She'd caught a glimpse in the trees, and knew exactly what it was. All she'd needed was to see it for a second to confirm her theory.


	4. Chapter 4

WARNING  
Offensive language used in this chapter.

"That gun won't do anything against it. Trust me."

"It?" The guy shouted. "He's just a bloody sociopath killing teens for fun."

She sighed. This guy was really enthusiastic.

Ignoring her warning, he carried on shooting it, and a horrible, twisted sound came from where he had just shot.

For some reason, that sound wasn't warning enough. He _still_ proceeded to shoot, the thing circling him as he did so.

Suddenly, out of nowhere, it jumped straight at him, teeth around the guy's neck, and sprinted off into the darkness that was creeping forward.

"Fuck." She said under her breath and ran after it as fast as she could, the others, fast on her trail.

Lily stopped and looked around. She couldn't see where they'd gone but doubted the man was still alive.

"Oh God…" Sam said.

She didn't understand what he meant until she saw it. The park ranger was slumped over a branch, high in the tree, covered in blood.

She closed her eyes, in a moment of silence, before turning to the boys.

"I think I know what we're dealing with." she said.

"Me too." replied Sam confidently, unlike Dean, who had no idea what was going on.

"Well don't tell everyone, guys!" He huffed, sarcastically.

"A wendigo. They…"

"Yes, I'm a hunter too Sam. I know what a wendigo is."

He interrupted Sam before he could finish, making Lily giggle, and Dean smile. But she had to remind herself, he's going to be dead soon, so don't get attached.

EDITOR'S NOTE

Sorry I haven't been very active, guys. I've been busy. But I will try to finish this part of the story before the end of July. Thanks so much for your support!

A reply to a review: I have taken into account your query about Lily's age, and have come up with a solution which will be revealed in a couple of chapters. Thank you, though, for pointing it out :) 3


	5. Chapter 5

"Ok. Let's think of this logically- we know it likes to hide in caves, so maybe we should split up and look around for one?"

Sam was obviously worried about the other two people we had trailing after us. They had no knowledge of monsters, which made them even more vulnerable, and probably didn't know how to work a gun. But Lily was going to make sure they survived. She believed that no innocent should die unnecessarily. Funny, considering she was working for the Devil.

Dean was first to volunteer the groups. "Great. So you and the lad; me and the ladies."

 _He wouldn't miss a chance to flirt with a girl._

"Sure," Sam said, stiffly, annoyed at how unfair Dean was making it.

"Okay." She said, smiling sweetly.

"Awesome," Dean added. And they split off in different directions.

Dean, Lily, and the oblivious girl walked steadily through the forest, but it wasn't long before they encountered the beast.

It was all was pretty brief, really. The monster was clearly no match for them, while they were out in the open, at least. An element of surprise was what they had needed, but lost it due to the Wendigo finding _them_. Fighting, and losing, against the monster, they were dragged into its dark, depressing, cave.

The other group, containing Sam and the other boy, did better, discovering them, and coming to the rescue while the monster was asleep.

Slowly, the group limped, carried, and dragged, themselves to the exit of the cave.

Time for the grand finally:

Lily cried out in pain as the monster, tamed gradually by some demons, dragged her away. She was taken to one of the complex's many caves, where she would wait and commit the crime. In conclusion, she let out a loud scream, as if she were being tortured, loaded her gun, and prepared for what her whole life had been leading up to.

Obviously, the boys chased after her. Never leaving anyone behind, seemed to be their motto, thankfully. Little did they know, the monster had been killed by the demons it had been raised with a couple of seconds ago, and they were racing against an imaginary clock that wouldn't have fatal results if the didn't get there in time.

"Lily!" Dean shouted. He sounded desperate, worried. Had he become attached? Hopefully not. She'd only ever experienced guilt once, and that was when she had had to kill a dog - she wasn't looking to feel that ever again.

How could someone so kind do something so wrong? She then thought.

They prevent the Apocalypse, a.k.a. The world's evolution, which goes against what both Heaven and Hell say.

She was even told, 'when good and evil agree, it must be the right answer'. It just baffled her, because normally, she could feel when someone was going to do something wrong. She could just sense it around them - the way they act. But not these guys. They had that 'good guy in the movies' kinda feel. That when they do something wrong it always turns out right.

The footsteps neared, a few more and they'd be in exact position.

She whispered a quick apology; then those footsteps came. Stood, right in front of her, were the two boys she was destined to kill. It was exhilarating. Her _whole life_ had led up to this. A massive amount of time, in which she'd filled with practice and rehearsal - playing the event, over and over in her head: Aim. Shoot. Shoot. Wait. Stab.

Their faces were the last thing she thought: concern, then shock. The final emotions they'd feel, before pain, of course.

 _Aim._

She lined the gun with Dean's forehead.

 _Shoot._

She pulled the trigger, the bullet flying towards its target.

 _Shoot._

She released the next bullet, and it sailed towards Sam's head.

 _Wait._

They needed to hit the floor before she could finish the job, before she could stab them, to make sure there wasn't any life left in them.

She waited, and waited, but it never came. The bang of their heads on the floor, the stab of her knife through their hearts. It never came.

Everything was frozen in time. Preventing the inevitable.

And then the command came. One she hadn't rehearsed. One she never thought she'd hear at an event like today. She heard it in her head, like thunder in the middle of the night:

 _Stop._

EDITOR'S NOTE

Hey, guys! Again, I'm sorry I haven't been very active, but I'm going to try post more and make the chapters longer! 3

A reply to a review: Hello! Thank you so much for your review, it really helped me to think about the characterisation and how I could make it better, I'll try to think about it next time, but obviously I'm not a professional writer so I apologise for giving you the wrong idea. Thanks again for your support, Lily. ;) x


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